A Freelancer’s Guide to Editors (by a Freelancer Turned Editor)

My day gig is editing CBS Man Cave Daily (no, not the other, crappier Man Cave Daily. The good one). One of my writers asked me for advice going full-time freelance and my advice is: WOAH! Have a spouse, because that is not something you want to do and also pay for health insurance, which for some reason gets more expensive the smaller the company you belong to.

But if you do go freelance in New York City, which I did, and only managed to drain an incredible amount of savings, this is my advice to him on how to dig up work and hang onto it. It’s based on what worked for me then and also what I’m most looking for now.

Don’t ask me how to become a Cracked columnist, though. I still have no idea how I got that lucky. The only reason Dan O’Brien and Robert Brockway aren’t dead of alcohol poisoning is they live too far away for me to buy them drinks every day.

I got into freelancing by asking a buddy of mine from publishing if he’d recommend me to his editor at AOL and he said sure. There’s so much editorial turnover that soon the boss who was sharing me with her co-editors had new co-editors, but the old ones were still hiring me at MTV and other companies.

Browse Mediabistro and stay away from Monster or Craigslist. Nobody on Craigslist wants to pay you what you’re worth. I can’t say anything about LinkedIn because I’ve never used it. Don’t write on a “based-on-page-views” amount unless it’s a backend bonus like we offer for a monthly top traffic bounty. Get paid for the actual work. Site’s a startup? !*(% you, pay me. Views are down this month? !*(% you, pay me. You offer valuable experience and exposure? !*(% YOU, PAY ME.

Getting work is really is as easy as just asking. Somebody, somewhere, is looking to hire you. You’re not going to waltz into Esquire and you hopefully won’t let a site reap your work without paying you in anything other than experience (you can always say no to terms. If they won’t barter remember you can always walk). But yeah, I consider pretty much everybody who e-mails me and I’m less concerned about their history and more concerned about the quality of their writing and ideas.

You would be AMAZED how many “professional” full-time men’s interest writers are godawful in every possible regard: sentence structure, grammar, spelling, deadlines, communication. I would trade nine of the commonly known bylines in this world of dude-blogging for one young woman with an interest in writing and the topic she’s writing about, because even if she has no plans to make a full career of it, I guarantee you she’ll make my life easy and she’ll probably pull 5x the traffic as the guy who just wants to write “The Five Beers You Drink in College.” I’ve done it and it’s a trade-up six times out of six. And the weird thing is how many writers like that either want to but think they can’t or never thought about doing an internet article full of jokes even though they’re giving it away for free on Twitter.

The tenth guy (or gal), though, he’ll be fantastic. That’s why you see names like Dan Seitz or (before he took an editorial gig) Ian Fortey everywhere on the web. They’re fast, funny, and fresh. Editors talk. We trade recommendations for writers because we can’t always give everyone all the work we want, but we’re still avaricious of our top talent.

Ask not what editors can do for you but show what you can do for editors. Most editors are overworked and just want to be sure their content is correct, catchy, and queued up.

Deliver more than is expected. Once you’ve got the work, give them the baker’s dozen. Is it due Tuesday? Have it in Monday. Did they expect it to be mildly funny? Make it hilarious. If an editor knows they’re going to get what they want but better you will always have work. That doesn’t mean 1000 words is better when the assignment is 800 but if those 800 require zero editing, editors will love you. My favorite writers to read aren’t just the best in terms of content, they’re also the best as an editor because there are no typos, no mistakes they should know better than to make. All I have to do is read and enjoy it, throw in links and images, and call it a day.

Some key areas in which a writer can demonstrate his/her value to an editor:

DEADLINES: If an editor knows they can rely on you (and again, even have it in early) you’ll get work.

EASE: Do you require a lot of editing? Do I have to remind you deadlines are coming up? Are you going to leave me waiting around the office at 7 p.m. when you promised I’d have it by 4?

ACCESS: Depending on the subject. There’s a guy who’s a huge pain in the neck to edit, but he gets great subjects to interview so I can never really cut ties. He’s not even a good interviewer, but he’s the one who’s going to get me subjects I can’t on my own. Or bring me story ideas I haven’t heard anywhere else yet.

To use a negative example: I just had a PR person call me at my desk (which I hate because even if it’s useful to me it’s a guaranteed two-to-ten minutes when I could glean all the info from an email in under 30 seconds) and go on and on and on about this thing she was pitching. And it’s like, “Lady…I don’t care. You called me. You wanted me to care. So make me care.” Even if I was intrigued I’d say “Great, send me the details in an email” because unless it’s a drop-everything opportunity, I guarantee I’m in the middle of something else when you call and I need to stay in that zone. And if I’m not intrigued I’ll still say “Okay, send me the details in an e-mail” just to get them off the phone.

Most freelancers are either artisans or factories. Artisans tailor their work to the site and usually rise up pretty fast. Editors want to get them before they’re out of reach with someone else who has more budget. Factories work for everybody and they’re not really writers. They excel at the side of the job that’s making contacts with publicists, sending out a vast flood of pitches to multiple sites. Then they just hammer out the product. They’re not worried about how it looks, they’re not worried about site voice. Writing’s the fastest part of their job. They’re never very smart. They’re just very determined. They ALWAYS *@^(ing argue with me when I reject a pitch, telling me why it would be a good idea and I should reconsider.

They have their relative worth, but in the long term I hate working with them. They always take more editing, and only half of them submit their work by deadline. They’re often sketchy and try to see what they can get away with. I had one who listed herself as one of our writers on her site and all her social media for months and months despite never selling me on a pitch. When she finally did sell me on one, she double-sold the article to another site than acted like she had no idea it would be a problem, although she might not have been acting because I guarantee she never read any of the documentation I sent her saying she couldn’t do that.

Don’t be a factory. Factories are people who write. Artisans are writers.

Editors can tell which one you’ll be almost out of the gate. When a new writer emails me I have different responses based on how much I actually want to take someone up on their inquiry of work, although I don’t reject anybody out of hand because I could be wrong. But you don’t want an editor thinking “Is this guy going to be more trouble than he’s worth?” You want them to feel like they’ve found a diamond mine nobody else knows about yet.

Read ClientsfromHell for a laugh and memorize the common problems you’ll encounter. Thankfully there’s less of it in the world of NYC’s corporate-backed blogging. But still.